My aunt (mother's middle sister) is about 30 years older than me. When I was in my teens and early 20s I used to have a lot of fantasies about her. She was good looking, about 5'5' with red hair and large breasts. Divorced twice, she had given up on any sort of social life when she got to her 40s. Even though she is older, she has kept in good shape but now wears a wig as her hair color has faded.
I'm self-employed and she was recently retired. Both my mother and my youngest aunt (her only two siblings) died about 10 years ago. Her youngest sister was her traveling companion, and since her death she has not gone anywhere. I decided to do a good deed and take her to Jamaica with me.
I have no idea what made me think I could pull this off, but I took my 'magic wand' back massager with me. It feels good after scuba diving to massage my legs. I don't usually take it with my on airplane trips because it weighs so much, but I was hoping to use it on my aunt. When I visit her (she lives about 500 miles from me in California), I often give her a light back rub which she likes. One thought led to the next.
Anyway, to cut a long story short, the second day I was there, I got up my nerve and asked her if she would like a back rub. She said she would, and, wearing shorts and a light blouse, got on her bed. She asked me what I had in my hand, and I told her what it was as I plugged it in. I started working on her back, and then went to her legs. I had never touched her so much and it was making me very horny. I guess the horniness made me a bit bolder.
I worked the massager up and down her legs, and asked her if it felt good, which she assured me it did. With one hand I rubbed her back and the other, with the wand, continued to work on her legs, working the massager higher and higher and my hand on her back lower and lower.
I put down the massager and spread her legs apart telling her I need to get to her inner thighs, which I then did, rubbing her up and down the inside of her thighs, gradually higher and higher. When I was all the way to the top of her legs, inside her thighs, I just held the massager in place. I absolutely could not believe this was actually happening, but indeed it was. I knew the massager was rubbing her pussy directly and this made me incredibly more horny. I started pushing her hips down with my other hand, just a bit so I wouldn't be too obvious.
I could hear her breathing increase in pace and I just held the massager there until I felt her tense up and release. I started moving the massager up and down her legs again, pretending that nothing had happened. A few minutes later she had recovered and told me that I could stop, that my hands must be getting tired. When she got up off the bed, her face was thoroughly flushed, which made me even hornier. As she got up to go the bathroom, I went back to my bedroom and relieved my own tensions.
That was the only time anything happened, but I am looking forward to our next trip. I am hoping to get my nerve up to give her another massage only this time I will get her to lie on her back. I want to 'massage' her breasts with my hands while using the massager between her legs. I am dying to see the look on her face when she starts to come.
I won't be able to take her on another trip for at least six months, but stay tuned, and I will post the experience if indeed anything happens.